Vacation rentals in Middletown

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Top-rated vacation rentals in Middletown

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
The spacious bedroom features a large adjustable split king bed with a premium mattress and crisp white bedding. Nightstands with lamps are positioned on either side of the bed, while a recliner is placed nearby. Natural light enters through the window, illuminating the neutral wall tones and carpet.
Guest suite in Liberty Township
4.98 out of 5 average rating, 115 reviews

Suite Liberty – Clean/Spacious

Our lower level, walk out suite (private entrance) has all you are looking for & more. The 1000 sf plus suite is spacious & comfortable. We are located on 2 peaceful acres in a residential area near the Liberty Way Exit off I-75. NOTE: If booking for December through February 28th. We will NOT have snow removal services. Snow melt & shovel will be available to our guests. Please check the weather before your arrival. The reservation can be cancelled 1 day prior to arrival with full refund

Top guest favorite
A light-colored couch is centered in the living area, complemented by a striped blue cushion. A glass coffee table rests on a patterned rug. A floor lamp and a side table fill the space, while a landscape painting adorns the wall, adding a touch of nature.
Apartment in Centerville
4.9 out of 5 average rating, 319 reviews

Apt 1: Octopus Garden in Uptown Centerville

This apartment is a twin to our 'Pilot Lounge' airbnb located across the hall. Two adults can sleep in a dedicated bedroom on a queen bed while your third guest sleeps on a twin roll-away bed. The kitchen is equipped for basic cooking with a fridge, Keurig, oven, microwave and toaster plus tableware. There's a 42" TV paired with an apple TV loaded with multiple apps. Alexa provides info and light control. Two window a/c keep the place cool. Free parking is available in the adjacent public lot.

Top guest favorite
The loft features exposed red brick walls and a raftered ceiling, creating a historic character. A spacious bed with a white coverlet is positioned beside two large windows with light curtains. A wooden table and chairs are situated in a cozy corner, complemented by decorative lighting.
Apartment in Lewisburg
4.96 out of 5 average rating, 175 reviews

Leader Loft

Conveniently located less than a mile from I-70 exit 14, on State Highway 503. This loft is perfect for any stay length for every occasion, and with the electronic door lock system it is perfect for a last minute stop as you’re traveling down the interstate. The Loft shares our building with Flour Bakery, coffee and gift shop, and is a minute's walk from a delicious bistro, antique shops, other gift shops, the library and hardware store. Come explore all that our quaint village has to offer!

Top guest favorite
An inviting living area features a large brown leather sofa, a patterned area rug, and a decorative coffee table atop wide plank wood floors. A cozy corner chair and a lamp add warmth, while the back wall showcases a mural with 'Centerville Carriage.'
Guesthouse in Centerville
5 out of 5 average rating, 242 reviews

The Carriage House in the Heart of Uptown

The Carriage House. Historic Charm with Modern Comfort. Built in 1897 and fully renovated in 2017, the Carriage House blends timeless character, with modern style & comfort, making it one of Centerville’s true hidden gems. Just steps from Uptown local restaurants, coffee shops and a scoop (or two) of Graeter’s Ice Cream. It’s perfectly located for your stay. Whether you’re planning a romantic weekend, visiting family, or simply looking to relax, this cozy retreat is the ideal place to unwind.

Top guest favorite
Guesthouse in Lebanon
4.95 out of 5 average rating, 458 reviews

Private carriage house on 3 acres!

New for 2024/2025... updated furniture with memory foam sleeper sofa, memory foam king and queen beds, additional twin mattress for floor for extra sleeping options. Outdoor conversation area! Bright and airy carriage house, located behind main house on 3 acres in Lebanon, Ohio. Close to downtown Lebanon, Springboro, Waynesville and short drive to Kings Island. -Kings Island 11 miles -Warren County Sports Park 7 miles -Roberts Center Wilmington 20 miles -Caesar Creek State Park 10 miles

Top guest favorite
The living area features wooden walls and a stone fireplace, complemented by soft-glow electronic candles. A cozy armchair is positioned near a window, while a round, textured coffee table sits at the center, adorned with a vase of dried flowers.
Guesthouse in Hamilton
4.99 out of 5 average rating, 237 reviews

Waterfront Cabin | Peaceful Pondside Escape

Seeking an escape for some peace and quiet? Welcome to The Little Cabin retreat, located on our 50-acre family farm in Ross, Ohio! Let us take you away from the distractions of life to a place where you can soak up nature in a cozy cabin, all within 30 minutes of downtown Cincinnati. You may fish in the lake if you'd like, or take a ride in the paddle boat, or simply enjoy sitting on the porch listening to the birds. Chances are, you may spot wild turkey or whitetail deer scampering by.

Guest favorite
A cozy sitting area features a modern black fireplace adorned with decorative candles. Two brown leather chairs are positioned beside a wooden side table, with a small potted plant nearby. Natural light streams in through the windows, illuminating the elegant rug and neutral wall tones.
Home in Madisonville
4.94 out of 5 average rating, 125 reviews

Tranquil Oasis 2BR/2BA with King Bed & Coffee Bar

Escape to our charming 2-bedroom, 2-bathroom Airbnb located in the serene suburbs of Cincinnati! Our home offers comfortable beds, a pillow bar to choose from, two clean full bathrooms, and a fully stocked kitchen. Unwind in the cozy living space or sip your morning coffee from our fully stocked coffee bar. Just a short drive from downtown Cincinnati, our Airbnb provides easy access to local shops, restaurants, and attractions while offering a quiet respite from the city bustle

Top guest favorite
A dining area features a wooden table set for four, complete with plates and glassware. Soft lighting is provided by a chandelier above. Dark leather chairs surround the table, and a sign with the word 'blessed' is mounted on the wall, complementing the modern kitchen visible in the background.
Apartment in Monroe
4.98 out of 5 average rating, 145 reviews

Newly Remodeled Two Bedroom rental unit

Newly Remodeled, Pet Friendly, King & Queen Beds, Washer&Dryer in unit, Smart TV's in every room, Alexa, Keyless Entry. For children: high chairs, Pack and Play's with thick mattresses, Air Mattress. 2 miles from I-75, Close to Kings Island, Miami Valley Gaming Casino, Flea Markets, Premium Outlet Mall, Centrally located between Dayton and Cincinnati, 30 minutes to Cincinnati Reds, Bengals, Dayton Dragons. Close to Lebanon Sports Complex & Warren County Sports Park

Top guest favorite
A cozy living area showcases two cream-colored couches positioned around a dark coffee table. Natural light enters through a large window, enhancing the space. A sleek ceiling fan is visible, and a small dining area is arranged with a table and two chairs against the wall.
Home in Miamisburg
4.95 out of 5 average rating, 193 reviews

The Linden Guesthouse - bike/hike/golf/shop/visit

This updated stylish 2 bed/1.5 bath single story guesthouse is perfect for work, group trips, fun, or family visits. The kitchen has dishes, cookware utensils, and pantry basics (oil, seasonings, sugar & flour). A Keurig single-serving and carafe coffee maker with k-cups and coffee filters is provided. The guesthouse has two living spaces, a dining room, a kitchen, a utility room with a washer and dryer, a private patio with outdoor seating, and a grill.

Guest favorite
A single-story house is depicted, featuring light-colored siding and a sloped roof. A two-car garage is present, with a neatly paved driveway leading to the entrance. Lush green grass surrounds the home, complemented by a leafless tree in the front yard.
Home in Middletown
4.9 out of 5 average rating, 203 reviews

New home & huge yard! 3-bd, 2 baths with game room

Enjoy our spacious master bedroom, brand new furniture, peaceful backyard with a 2 person hot tub, BBQ grill, fully equipped kitchen, game room, convenient parking, and 3 spacious bedrooms. We have everything you need to stretch your legs and relax. Ideal for visiting sights in Cincinnati (25 min) or Dayton (15 min) as well as King's Island (15 min). Close to shops, restaurants, and entertainment. Kids and families are welcome!

Guest favorite
A living room is depicted with a television mounted on a wooden stand, flanked by two comfortable reclining chairs and a sectional sofa. An aviation-themed artwork hangs above, while a sleek, metal coffee table adds a modern touch. Natural light enters through windows with light blinds.
Home in Middletown
4.92 out of 5 average rating, 112 reviews

5 Minute Call

"5 Minute Call" is located next to the Middletown Regional Airport (home of ​Start Skydiving) and Smith Park. ​ The house is a 1 minute walk to the airport, 2 minute walk to Smith Park, 23 min drive to Spooky Nook, 29 min drive to Miami University Oxford. With an arcade set-up in the basement, large kitchen dining table, and theatre-like living room, the house has multiple rooms for gathering with friends and family.

Top guest favorite
The exterior of a single-story brick home is shown, featuring a double garage, manicured lawn, and flower beds with yellow blooming flowers. A driveway leads up to the home, surrounded by peaceful greenery and trees in the background.
Apartment in Middletown
5 out of 5 average rating, 151 reviews

SouthView Acres (No Hidden Fees!)

We are ready to welcome you to SouthView Acres! Enjoy a comfortable stay in our mother-in-law suite with its own private entrance. Private parking, quiet location and minutes away from I75 access. Enjoy cable TV and wifi. Our home is on 10 acres where you are welcome to walk the trails or warm yourself by the fire pit at night. A convenient location for business or pleasure travelers. No hidden fees.

Popular amenities for Middletown vacation rentals

When is the best time to visit Middletown?

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Frequently Asked Questions

  • Are there family-friendly vacation rentals in Middletown?

    Middletown has more than 40 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do house rentals in Middletown have free parking?

    Absolutely! We offer over 30 house rentals with free parking in Middletown. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Middletown have air conditioning?

    Absolutely! We offer over 10 apartment rentals with air conditioning in Middletown. Enjoy a tailored experience with all the comforts you desire.

  • How much does it cost to stay in apartment rentals in Middletown?

    Experience the best of Middletown with our apartment rentals, starting at about $70 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Where should I stay in Middletown?

    Make yourself at home in Middletown by choosing from our most frequently booked neighborhoods. We have over 50 vacation rentals in Mayfield, over 10 vacation rentals in Avalon, and over 50 vacation rentals in Oakland.

  • Are there vacation rentals with a dedicated workspace in Middletown?

    Yes! Work meets play with ease at over 20 vacation rentals in Middletown featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Middletown?

    Four-legged friends are welcome in Middletown. Choose from more than 10 vacation rentals for guests traveling with pets.

  • Do house rentals in Middletown have wifi?

    Absolutely! We offer over 30 house rentals with wifi in Middletown. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Middletown have a kitchen?

    Absolutely! We offer over 10 apartment rentals with a kitchen in Middletown. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for House Rentals in Middletown?

    Enhance your stay in our House Rentals with the most popular amenities: over 30 homes with free parking, over 30 homes with wifi, over 30 homes with a kitchen, over 30 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about vacation rentals in Middletown

  • Total vacation rentals

    Explore 60 vacation rentals in Middletown

  • Nightly prices starting at

    Middletown vacation rentals start at € 17 per night before taxes and fees

  • Verified guest reviews

    Over 1,470 verified reviews to help you choose

  • Family-friendly vacation rentals

    40 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    60 of Middletown vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Middletown rentals

  • 4.8 Average rating

    Middletown stays are highly rated by guests—averaging 4.8 out of 5!

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